Trimethyl((tributylstannyl)ethynyl)silane → HCID 68814361, compound

HRID 729228Notes

Reaction equation

HRID 729228 reaction equation
Br[C:2]1[C:3]([C:7]([NH2:9])=[O:8])=[CH:4][S:5][CH:6]=1.C([Sn]([C:23]#[C:24][Si:25]([CH3:28])([CH3:27])[CH3:26])(CCCC)CCCC)CCC>>[CH3:26][Si:25]([C:24]#[C:23][C:2]1[C:3]([C:7]([NH2:9])=[O:8])=[CH:4][S:5][CH:6]=1)([CH3:28])[CH3:27]

Participants

3

Reactant 2

HCID 639663Trimethyl((tributylstannyl)ethynyl)silaneHCID 189381394-Bromothiophene-3-carboxamide

Product 1

HCID 68814361HCID 68814361, compoundYield 27.7%

Procedure

The product from step B (1 g), tributylstannyl(trimethylsilyl)acetylene (2.16 g) and palladium(tetrakis)triphenylphoshine (0.28 g) were placed into degassed toluene (20 ml) and the mixture was heated under reflux for 16 hours under an atmosphere of nitrogen. After cooling, the solvent was removed and the residue was chromatographed on silica gel (hexane:ethylacetate 3:1). After three consecutive crystallisations from hexane, 0.3 g of 4-(trimethylsilyl)ethinyl-3-thiophene formamide was obtained (m.p. 90-94° C.).

Workup

  1. custominto degassed toluene (20 ml)
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 16 hours under an atmosphere of nitrogen
  4. temperatureAfter cooling
  5. customthe solvent was removed
  6. customthe residue was chromatographed on silica gel (hexane:ethylacetate 3:1)
  7. customAfter three consecutive crystallisations from hexane

Sources & evidence

ORD record
ord-c2f06b1b271c4f27a58c948505154d41
Source dataset
uspto-grants-2009_09
Patent number
US07582589B2

Reaction notes

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